Prominent members of a Massachusetts Democratic fund-raising network that boosted Barack Obama in 2008 and Deval Patrick two years earlier are hosting high-dollar events for presidential candidate Martin O’Malley on Tuesday.

The bulk of the state’s Democratic establishment, which splintered in 2008 between Obama and then-Senator Hillary Rodham Clinton, has coalesced thus far behind Clinton.

But the three events in the Boston area reflect a residual disenchantment with the Democratic front-runner among some of the party’s local power brokers.

Diddy Cullinane and John Cullinane, the software magnate, are hosting an evening event for O’Malley, the former Maryland governor, at the Dedham Country and Polo Club, where attendees are asked for up to $5,400, according to an invitation obtained by the Globe.

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That follows an afternoon fund-raiser on Boylston Street headlined by close Patrick allies such as Joshua Boger, Amy Boger, and Sean Curran, which carries the same asking price.

O’Malley is also holding a luncheon fund-raiser at the Mintz Levin law firm, where access runs up to $1,000.

O’Malley so far has yet to make much of a dent in the Democratic primary polls, trailing both Clinton and US Senator Bernie Sanders of Vermont.

But the dynamics between the Clintons and supporters of Obama and Patrick have long been complicated, after Obama’s upstart run against Clinton in 2008, which Patrick — along with other top Massachusetts Democrats like Edward M. Kennedy and John F. Kerry — endorsed.

Tuesday’s events come as Sanders, a socialist, has carved out something of a niche as the liberal alternative to Clinton — a lane O’Malley backers had hoped he would fill.

The Cullinanes are longtime contributors to Democratic causes. Diddy Cullinane was an early Obama supporter, having made contributions to both his 2004 Senate race and, in late 2007, his presidential campaign, according to federal campaign finance documents.

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John Cullinane helped pave the way for Massachusetts’ software industry and has since helped tech companies in Ireland through the Cullinane Group. The couple were also longtime family friends with the late senator Kennedy.

Boger was a prominent Patrick backer during his gubernatorial campaigns and his tenure in office, and he helped Patrick craft the idea for his post-politics career in venture capital. The Vertex Pharmaceuticals founder has been a heavy political contributor for years, giving mostly to Democratic causes, including to Obama in 2007. Federal Election Commission records show that Boger has made nearly $290,000 in federal political contributions since 2000.

Amy Boger has donated nearly $79,000 since 2006, records show.

Curran, who cochaired Patrick’s campaign finance committee during his successful reelection bid in 2010, is a state lobbyist who helped unveil Patrick’s official gubernatorial portrait in January.

The Boylston Street event is cohosted by, among others, Colette Phillips, a Boston public relations executive who was also an early donor to Obama and Patrick, according to federal and state campaign finance records. Private equity executive David Belluck, a heavy Obama fund-raiser who has helped O’Malley build his Massachusetts network in the past, is also among the cohosts.